Electrophilic Aromatic Chlorination: Synthesis of the Fungicide Chloroneb

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 16 (2011) pp 89-90

Electrophilic Aromatic Chlorination: Synthesis of the Fungicide Chloroneb

Gary W. Breton

Berry College, Department of Chemistry, PO Box 495016, Mount Berry, GA 30149 gbreton@berry.edu
Received January 23, 2011. Accepted March 1, 2011.

Published: 18 March 2011

Abstract. A convenient laboratory synthesis of the widely-used fungicide Chloroneb (i.e., 1,4-dichloro-2,5-dimethoxybenzene) is described. The experiment illustrates the practical utility of the synthetically important process of electrophilic aromatic substitution. The electrophile, chlorine, is generated in-situ via the reaction of calcium hypochlorite with acetic acid. The Chloroneb product is obtained in yields averaging 37%.

Key Words: Laboratories and Demonstrations; organic chemistry; synthesis

(*) Corresponding author. (E-mail: gbreton@berry.edu)

Article in PDF format (34 KB) HTML format

Supporting Materials:

Equipment list, chemicals and CAS registry numbers, safety and hazard notes, instructor notes, student lab experiment hand-out, ¹H NMR and IR spectra of the product (919 KB).